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New sertraline analogue, preparation method and applications thereof

A kind of analog, technology of sertraline, applied in the field of compound and preparation thereof

Active Publication Date: 2019-12-31
北京安博睿达医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the activity of sertraline still needs to be further improved

Method used

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  • New sertraline analogue, preparation method and applications thereof
  • New sertraline analogue, preparation method and applications thereof
  • New sertraline analogue, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] Embodiment 1: preparation compound 1

[0097]

[0098] Add the compound of formula 1-S (12g, 0.035mol, 1eq) into a 250ml single-necked flask, and 150ml of water as a solvent. Under stirring, add excess potassium carbonate to it, and stir at room temperature for 1-2h.

[0099] Post-processing: extract with 200ml*2EA, dry over anhydrous magnesium sulfate, concentrate by suction filtration, and obtain 10.9g of pure product, which is directly used in the next step without post-processing.

[0100]

[0101] Add the above-mentioned pure product (10.9g, 0.0356mol, 1eq) into a 250ml two-necked flask, 100ml of a mixed solvent of methanol and tetrahydrofuran (volume ratio 1:1) as a solvent, and add 1-ethoxy-1 Trimethylsilylcyclopropane (7.5g, 0.0427mol, 1.2eq) and acetic acid (4.3g, 00712mol, 2eq), and finally, sodium cyanoborohydride (4.5g, 0.0712mol, 2eq) was added in portions, and the addition was complete Then, heat to reflux overnight.

[0102] Cool to room temperatu...

Embodiment 2

[0107] Embodiment 2: drug activity test

[0108] 2.1 Determination of antidepressant activity by mouse tail suspension test

[0109] Male ICR mice (SPF grade), weighing 18-22g, attach a clip to the center rope of the top plate of a 25×25×25cm tail-suspension box, clamp the mouse’s tail tip 1cm to make it hang upside down, and the head is 4-5cm away from the bottom of the box . A certain dose (24 mg / kg) of the exemplary compound of the present invention, sertraline, and 0.5% sodium carboxymethylcellulose solution was ground to prepare a suspension for use. Different doses of samples to be tested were orally administered 60 minutes before the experiment, and the tail was suspended for 6 minutes after administration, and the immobility time of the mice was accumulated for 4 minutes after the experiment. The results are shown in Table 2.

[0110] 2.2 Determination of antidepressant activity by forced swimming test in mice

[0111] Male ICR mice (SPF grade), weighing 18-22 g, w...

Embodiment 3

[0114] Acute Toxicity Study of Exemplary Example Compounds of Example 3

[0115] Experimental Materials:

[0116] ICR mice, half male and half female, weighing 18-22 g, were fed with pellet feed, and had free access to food and water.

[0117] The compounds tested in Table 2 were respectively prepared into suspensions with a concentration of 500 mg / mL with 0.5% CMC-Na.

[0118] experimental method

[0119] The ICR mice were given the compounds tested in Table 2 at a dose of 10 ml / kg by body weight once, and the toxicity and death of the animals within 14 days after administration were observed. It was found that after a single intragastric administration of the mice, the mice moved sluggishly, lay still and moved less, and returned to normal after 40-60 minutes. Within 14 days after the administration, the mice did not die. On the 15th day, all the mice were sacrificed, dissected, and all organs were inspected with the naked eye, and no obvious lesions were found.

[0120]...

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Abstract

The invention belongs to the technical field of compounds, preparation methods and applications thereof, and specially relates to a sertraline analogue or a pharmaceutically acceptable salt thereof, wherein the sertraline analogue has a structure represented by the following formula (I), and the compound has good pharmaceutical activity compared with sertraline. The invention further provides a preparation method and applications of the compound represented by the formula (I).

Description

technical field [0001] The invention relates to a new sertraline analogue and its preparation method and application, and belongs to the technical field of compounds and its preparation method and application. Background technique [0002] Sertraline [chemical name (1S-cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthyridineamine (structural formula such as Formula (I-M))] or sertraline hydrochloride (also referred to as sertraline) [chemical name (1S-cis)-4-(3,4-dichlorophenyl)-1,2,3, 4-tetrahydro-N-methyl-1-naphthyridinamine hydrochloride (the structural formula is shown in formula (II-M))]: [0003] [0004] Sertraline is indicated for the treatment of symptoms associated with depression, including depression associated with anxiety, with or without a history of mania; also for the treatment of obsessive-compulsive disorder. [0005] However, the activity of sertraline still needs to be further improved. Contents of the invention [0006] The object...

Claims

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Application Information

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IPC IPC(8): C07C211/42C07C215/08C07C217/08C07C323/23C07C323/25C07D295/13C07D205/04C07D213/38C07D237/20C07D241/20C07D239/26C07D207/32C07D333/20C07D307/36C07D277/28C07D233/64C07D263/32C07D277/64C07D263/56C07D235/14C07D209/14C07D471/04C07D215/12C07D241/42C07D239/74C07D319/18C07D317/58A61K31/135A61K31/145A61K31/4453A61K31/5375A61K31/495A61K31/397A61K31/40A61K31/4402A61K31/4406A61K31/4409A61K31/4965A61K31/50A61K31/505A61K31/381A61K31/341A61K31/4164A61K31/4184A61K31/426A61K31/421A61K31/404A61K31/47A61K31/472A61P13/10A61P25/00
CPCC07C211/42C07C215/08C07C217/08C07C323/23C07C323/25C07D295/13C07D205/04C07D213/38C07D237/20C07D241/20C07D239/26C07D207/32C07D333/20C07D307/36C07D277/28C07D233/64C07D263/32C07D277/64C07D263/56C07D235/14C07D209/14C07D471/04C07D215/12C07D241/42C07D239/74C07D319/18C07D317/58A61P13/10A61P25/00C07C2601/02C07C2602/10C07B2200/07
Inventor 闫京波李松钟武肖军海王刚
Owner 北京安博睿达医药科技有限公司
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